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Sailing and catamaran holidays and cruises in Sicily

Exploring the Sicilian coastline by sailboat is a journey between the magic of San Vito lo Capo and the wild beauty of the Zingaro Reserve. The turquoise waters of the Tyrrhenian Sea frame majestic cliffs and secret bays, offering a sailing experience wrapped in an unparalleled natural setting. Every moment is an opportunity to discover the true essence of Sicily, a blend of ancient charm and unspoilt landscapes that leave an indelible imprint on the hearts of those who sail there.

Why book a holiday with Sailsquare?

The world's largest marketplace for sailing holidays

The world's largest marketplace for sailing holidays

80,000 travellers have already chosen their holiday from a catalogue of 12,000 proposals in 120 destinations, worldwide.

Get onboard solo, with your family or your friends

Get onboard solo, with your family or your friends

Book a single spot, a cabin or the whole boat just for yourself, or for your friends or family.

Find out before you book who's waiting for you on board

Find out before you book who's waiting for you on board

Find out more about the skipper and travellers who have already booked the holiday, to find out more about the

Sailing holidays that suit all budgets

Sailing holidays that suit all budgets

On Sailsquare, sailing holidays are within everyone's reach. Thousands of proposals to choose from, at affordable prices.

Reviews - Sailing and catamaran holidays and cruises in Sicily

43 reviews

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Ten days from Catania to the Aeolian Islands on a luxury sailboat

08/27/2025

Marta B.

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Italy

It was my first sailing holiday and I will always carry these 10 days in my heart! :) The skippers Paco and Gabriella were very helpful, kind and attentive, able to convey their passion for the sea and create that special atmosphere that makes you feel immediately at home. The boat was very beautiful and with all the comforts for a relaxing holiday. The navigation was wonderful, with the wind and the sea giving a feeling of absolute freedom, the spectacular sunsets seen from the boat and even the unique experience of crossing the Strait of Messina under sail! The trip was made even more enjoyable by the delicious food and sharing moments on board, as well as the company of wonderful people I met. A holiday that made me fall in love with life on a boat and that I recommend to anyone who wants to discover the Aeolian Islands, Sicily and even a piece of Calabria from an authentic and magical perspective.
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Ten days from Catania to the Aeolian Islands on a luxury sailboat

08/26/2025

Mario L.

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Italy

FABULOUS holiday, and to say it a demanding Milanese..... the two "captains" Gabriella and Paco are delightful people, prepared, kind, attentive and truly dedicated to the well-being and happiness of the crew. We also did some sailing school and "introduction" to life as a boat, always maintaining the highest standards of marine safety. The destinations we reached were of greatest interest to me: Tropea, Panarea, the Archaeological Museum of RC (with the Bronzes...), the ascent to the volcano of Vulcano and others. They always tried to make us try bays, inlets and always varied experiences, without sparing themselves in the slightest! We sailed as often as we could! Gabriella also not only knows how to prepare excellent dishes but encourages the crew to propose and prepare new ones. Really nice people with whom to have a nice chat. We had a really great time also helped by luck, the crew was fantastic! I RECOMMEND [hidden] Sailing ABSOLUTELY! PS boat TOP!!
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Crossing to the northwest: sailing weekend in Sicily

06/6/2025

Lisa N.

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Italy

Weekend at the end of May really nice with Antonio and Bianca! Everything was perfect, from their great experience at sea to the kindness and family atmosphere. The boat is a gem, kept with care and love. They are two true lovers of the sea, with a lot of experience. Absolutely recommended 🥰
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Mini cruise Syracuse - Marzamemi with hostess and galley included

09/30/2024

Francesco C.

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Italy

Capitano e hostess fantastici! Una bellissima avventura immersiva nel mare e nel sole!

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